1. Field of the Invention
This invention relates to new keto-peroxy compounds containing at least one keto group and at least one peroxy group, each peroxy oxygen being joined to a tertiary carbon atom. Also, the invention relates to a process for making the aforesaid keto-peroxy compounds.
2. Description of the Prior Art
In U.S. Pat. No. 2,508,256 (May 16, 1950), Harman disclosed the reaction of hydroperoxides with unsaturated compounds containing an olefinic non-conjugated double bond and containing a "meta-directing" group attached to one of the carbon atoms of the double bond, in the presence of an alkaline-reacting compound. A wide variety of unsaturated compounds are listed to illustrate the compounds operable under the invention, including unsaturated ketones, among others. Included in the list of ketones were methyl vinyl ketone, propenyl allyl ketone, vinyl benzyl ketone, phorone and mesityl oxide. In the working examples, however, there was no statement to the type of peroxidic product which resulted from the reaction of hydroperoxides with unsaturated ketones such as mesityl oxide or phorone.
Work by Yang and Finnegan [J. Am. Chem. Soc., 80, 5845 (1950)] showed that contrary to the assertions of Harman, the products obtained from the reactions of .alpha.,.beta.-unsaturated ketones with hydroperoxides under alkaline conditions were epoxyketones, not peroxyketones. Furthermore, under these conditions isophorone failed to react and this was explained to be the result of a conformationally unfavorable structure. This method of preparing epoxyketones is the subject of U.S. Pat. No. 3,062,841 (Nov. 6, 1962).